Sulphonated thianthrenes useful as pharmaceutical compounds



' Patented June 22, 1926. v

UNI-TED STATESIVPATENT OFFICE.

HEINRICH HERMINGHAUS, OF ELBERFELD, GERMANY, ASSIGNOB, BY MESNE ASSIGN- MENTS, TO WIN'IHROP CHEMICAL COMPANY, INC., 01 NEW YORK, N. Y., A COB- IOBA TION OF NEW YORK.

SULPHONA'IED THIANTHBENES USEFUL AS PHARMACEUTICAL COMPOUNDS.

No Drawing. Application filed May 24, 1924, Serial No. 715,687, and in Germany Augult 4, 1928. i

The present invention relates to the manucoloration. They show a strong antifacture and production of new sulphonated phlogistical action and precipitate albuthianthrenes useful as pharmaceutical commen, when used in a weakly acid solution. pounds. They are obtainable by treating In carrying out the invention practically 5 with sulphonating agents, such as sulphuric I can proceed as follows, the parts being by acid, fuming sulphuric acid, or the chloroweight:- hydrin of sulphuric acid, thianthrene and 1000 parts of dimethylthianthrene are its substituted products or the compounds heated with 460 parts of pure sulphuric obtainable according to the United States acid during 8 hours at 100 C. then for 10 10 Letters Patents No. 1,426,430 and No. 1,427; hours at 120 C. and finally for 8 hours at 182 at a high temperature until the reaction 150160 C. until a test portion iscomproducts may be completely dissolved in pletely soluble in water. The product thus water. The products obtainable according obtained is as hard as glass. It is dissolved to these patents are thick oily liquids, min water and this solution is then neutrall5 soluble in water, obtained by treating the ized with sodium carbonate and evaporated homologues of benzene with. sulphurand 'to dryness. The roduct is after being aluminum chloride. dried and pulverize a dark brown powder The new products are monosulphonic and is capable of precipitating to albumen. acids and may be represented by the gen- I claim:

20 eral formula I 1., As a new product a monosul honated thianthrene the sodium salt of WhlCh has a \/s i strong antiphlogistical action and in its (1 l pulverized form is a'brownish powder rea \/\s i 11y soluble in water with aidark reddishbrown coloration. .in which the thianthrene nucleus may be 2. As a new producta dimethyl-thiansubstituted or unsubstituted and in which throne monosulphonic sued the sodium salt the position of the SO ,H group is undeterof which has a strong antiphlogistical acmined. tion and in its dry pulverized form is a The new products are after being dried dark brown powder.

and pulverized in the form of their alkaline In testimony whereof I have hereunto salts generally brownish powders, easily set my hand. soluble in water with a dark reddish-brown HEINRICH HERMINGHAUS. 

